Director,CustomerSuccessDataEngineering

Role Overview This role serves as the data leader and technical authority for Customer Success data at Toast. You will own the strategy and execution of CS data modeling initiatives -- redesigning the CS data model from the ground up and defining how data is accessed, queried, and served across the organization. The CS data model needs to work reliably in two modes: as a structured foundation for dashboards, reporting, and operational metrics, and as a well-documented, trustworthy layer that AI systems can query consistently. Building for both -- and making deliberate architectural decisions about when each approach is appropriate -- is central to this role. This is an embedded role, sitting inside the CS organization. CS data problems are business problems first -- understanding how customers are being supported, where friction exists, and what patterns predict risk or opportunity requires close proximity to the teams asking those questions. This role is positioned to build that context directly and translate it into data architecture decisions. You will lead a small team of two senior data and analytics engineers to start, with room to grow as the function matures. What You'll Do Data Architecture & AI Data Strategy Own the redesign of the unified CS data model, connecting data across Care, CX, Enablement, and CSS teams and source systems including our new contact center platform. Define and execute the AI data strategy for CS -- specifically, how AI accesses, queries, and interacts with the data model. This means making active architectural decisions about when to pre-calculate and structure data versus when to allow dynamic AI retrieval, with predictability and consistency of outputs as the governing constraint. Build and maintain a documentation layer that functions as a first-class artifact -- not an afterthought. Reliable AI data access depends on well-structured, accurate documentation, and this person will treat it that way. Develop and apply a clear framew